Facile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer

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Facile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer is …
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scholarly articleQ13442814

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P356DOI10.1016/J.BMCL.2014.07.091
P932PMC publication ID4163096
P698PubMed publication ID25172419

P2093author name stringJason R Buck
H Charles Manning
Dewei Tang
Michael L Nickels
Yiu-Yin Cheung
P2860cites workTranslocator protein (18kDa): new nomenclature for the peripheral-type benzodiazepine receptor based on its structure and molecular functionQ24296269
An 18-kDa translocator protein (TSPO) polymorphism explains differences in binding affinity of the PET radioligand PBR28Q24599479
Regulation of translocator protein 18 kDa (TSPO) expression in health and disease statesQ24631648
Involvement of peripheral benzodiazepine receptor in the oxidative stress, death-signaling pathways, and renal injury induced by ischemia-reperfusionQ28564914
Advanced MRI and PET imaging for assessment of treatment response in patients with gliomasQ33655854
Treatment response evaluation using 18F-FDOPA PET in patients with recurrent malignant glioma on bevacizumab therapyQ33838502
Inducible loss of one Apc allele in Lrig1-expressing progenitor cells results in multiple distal colonic tumors with features of familial adenomatous polyposis.Q33840012
Molecular imaging of gliomas with PET: opportunities and limitationsQ33961188
SSR180575 (7-chloro-N,N,5-trimethyl-4-oxo-3-phenyl-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide), a peripheral benzodiazepine receptor ligand, promotes neuronal survival and repairQ34129717
Role of peripheral benzodiazepine receptors in mitochondrial, cellular, and cardiac damage induced by oxidative stress and ischemia-reperfusionQ34224014
Rapid, Microwave-Assisted Organic Synthesis of Selective (V600E)BRAF Inhibitors for Preclinical Cancer ResearchQ34488278
Quantitative, preclinical PET of translocator protein expression in glioma using 18F-N-fluoroacetyl-N-(2,5-dimethoxybenzyl)-2-phenoxyanilineQ34522608
Imaging of a glioma using peripheral benzodiazepine receptor ligandsQ34594710
Synthesis and structure-activity relationships of 5,6,7-substituted pyrazolopyrimidines: discovery of a novel TSPO PET ligand for cancer imagingQ34632108
The peripheral benzodiazepine receptor: a promising therapeutic drug targetQ35181304
Preclinical imaging evaluation of novel TSPO-PET ligand 2-(5,7-Diethyl-2-(4-(2-[(18)F]fluoroethoxy)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)-N,N-diethylacetamide ([ (18)F]VUIIS1008) in gliomaQ35213599
Quantitative preclinical imaging of TSPO expression in glioma using N,N-diethyl-2-(2-(4-(2-18F-fluoroethoxy)phenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)acetamide.Q36081687
Influence of TSPO genotype on 11C-PBR28 standardized uptake valuesQ37087243
The translocator proteinQ37865972
Molecular imaging of the translocator protein (TSPO) in a pre-clinical model of breast cancerQ39769015
In vivo TSPO imaging in patients with multiple sclerosis: a brain PET study with [18F]FEDAA1106.Q40275502
Targeted molecular imaging agents for cellular-scale bimodal imagingQ40491443
Binding characteristics of SSR180575, a potent and selective peripheral benzodiazepine ligandQ40627579
Involvement of the peripheral benzodiazepine receptor in the development of rheumatoid arthritis in Mrl/lpr miceQ40701449
Comparison of 18F-FDG and 11C-methionine for PET-guided stereotactic brain biopsy of gliomasQ42465912
TNF-alpha induced PMN apoptosis in whole human blood: protective effect of SSR180575, a potent and selective peripheral benzodiazepine ligandQ42973988
Involvement of the peripheral benzodiazepine receptor in the development of cutaneous pathology in Mrl/Lpr miceQ44264744
Ligands of the peripheral benzodiazepine receptor have therapeutic effects in pneumopathies in vivoQ44563789
In vivo imaging of the 18-kDa translocator protein (TSPO) with [18F]FEDAA1106 and PET does not show increased binding in Alzheimer's disease patientsQ48151150
Dynamic 18F-FET PET in newly diagnosed astrocytic low-grade glioma identifies high-risk patients.Q53084430
In vivo imaging of neuroinflammation in the rodent brain with [11C]SSR180575, a novel indoleacetamide radioligand of the translocator protein (18 kDa).Q53267275
Brain TumorsQ60618613
Targeted imaging of colonic tumors in smad3-/- mice discriminates cancer and inflammationQ80140819
P433issue18
P407language of work or nameEnglishQ1860
P304page(s)4466-4471
P577publication date2014-08-08
P1433published inBioorganic & Medicinal Chemistry LettersQ2709483
P1476titleFacile synthesis of SSR180575 and discovery of 7-chloro-N,N,5-trimethyl-4-oxo-3(6-[(18)F]fluoropyridin-2-yl)-3,5-dihydro-4H-pyridazino[4,5-b]indole-1-acetamide, a potent pyridazinoindole ligand for PET imaging of TSPO in cancer
P478volume24

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cites work (P2860)
Q39181546Evaluation of TSPO PET Ligands [18F]VUIIS1009A and [18F]VUIIS1009B: Tracers for Cancer Imaging
Q41446521New structure-activity relationships of N-acetamide substituted pyrazolopyrimidines as pharmacological ligands of TSPO.
Q55456900Preclinical Evaluation of a Novel TSPO PET Ligand 2-(7-Butyl-2-(4-(2-[18F]Fluoroethoxy)phenyl)-5-Methylpyrazolo[1,5-a]Pyrimidin-3-yl)-N,N-Diethylacetamide (18F-VUIIS1018A) to Image Glioma.
Q35827097Preclinical TSPO Ligand PET to Visualize Human Glioma Xenotransplants: A Preliminary Study
Q38809524Translocator protein (TSPO) ligands for the diagnosis or treatment of neurodegenerative diseases: a patent review (2010 - 2015; part 2).
Q62862505[F]FEPPA: Improved Automated Radiosynthesis, Binding Affinity, and Preliminary in Vitro Evaluation in Colorectal Cancer

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